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The Obstacle is the Way by Ryan Holiday

modified 2018/11/02

Book notes for “The Obstacle is the Way”, The Ancient Art of Turning Adversity to Advantage by Ryan Holiday

Quick review:

A quick read covering stoic thinking and how it can be applied to one’s
life. Lots of examples and repetition, but that did not bother me as
this tends to be necessary to really get people to internalise the
lessons from this sort of book. Sure, it could be condensed to 50 pithy
quotes, but reading those quotes would not have the same effect as
reading this book. The ideas feel familiar, in a good way, and appeal to
me. I am sure that applying them would make me a better and more
effective person. I will definitely read some Meditations and Senneca
after this, and try and apply many of the highlighted ideas

Questions raised:

To get more detail on these ideas, go to the source, and read
Meditations and Letters from a Stoic (Senneca) next. There are many
interesting ideas in the book that it would be good to get more angles
on, so as to really burn them into my brain (or reject).

Insights, lessons learnt:

read more about stoicism

try and perceive your life from the outside when unsure of how to
resolve an issue

It’s not just: How can I think this is not so bad? No, it is how to will
yourself to see that this must be good-an opportunity to gain a new
foothold, move forward, or go in a better direction. Not “be positive”
but learn to be ceaselessly creative and opportunistic. Not: This is not
so bad. But: I can make this good. location 191

Many of our problems come from having too much: rapid technological
disruption, junk food, traditions that tell us the way we’re supposed to
live our lives. We’re soft, entitled, and scared of conflict. Great
times are great softeners. Abundance can be its own obstacle, as many
people can attest. location 228

This insight lives on today in Warren Buffet’s famous adage to “be
fearful when others are greedy and greedy when others are fearful.”
Rockefeller, like all great investors, could resist impulse in favor of
cold, hard common sense. location 291

through our perception of events, we are complicit in the creation-as
well as the destruction-of every one of our obstacles. There is no good
or bad without us, there is only perception. There is the event itself
and the story we tell ourselves about what it means. location 384

Don’t forget, there are always people out there looking to get you. They
want to intimidate you. Rattle you. Pressure you into making a decision
before you’ve gotten all the facts. They want you thinking and acting on
their terms, not yours. So the question is, are you going to let them?
location 416

So go ahead, feel it. Just don’t lie to yourself by conflating emoting
about a problem and dealing with it. Because they are as different as
sleeping and waking. location 480

Subconsciously, we should be constantly asking ourselves this question:
Do I need to freak out about this? And the answer-like it is for
astronauts, for soldiers, for doctors, and for so many other
professionals-must be: No, because I practiced for this situation and I
can control myself. Or, No, because I caught myself and I’m able to
realize that that doesn’t add anything constructive. location 498

Objectivity means removing “you”-the subjective part-from the equation.
Just think, what happens when we give others advice? Their problems are
crystal clear to us, the solutions obvious. Something that’s present
when we deal with our own obstacles is always missing when we hear other
people’s problems: the baggage. With other people we can be objective.
location 536

Take your situation and pretend it is not happening to you. Pretend it
is not important, that it doesn’t matter. How much easier would it be
for you to know what to do? How much more quickly and dispassionately
could you size up the scenario and its options? location 541

Having learned early in life that reality was falsely hemmed in by rules
and compromises that people had been taught as children, Jobs had a much
more aggressive idea of what was or wasn’t possible. location 711

So many people in our lives have preached the need to be realistic or
conservative or worse-to not rock the boat. This is an enormous
disadvantage when it comes to trying big things. Because though our
doubts (and self-doubts) feel real, they have very little bearing on
what is and isn’t possible. location 721

This is radically different from how we’ve been taught to act. Be
realistic, we’re told. Listen to feedback. Play well with others.
Compromise. Well, what if the “other” party is wrong? What if
conventional wisdom is too conservative? It’s this all-too-common
impulse to complain, defer, and then give up that holds us back. An
entrepreneur is someone with faith in their ability to make something
where there was nothing before. To them, the idea that no one has ever
done this or that is a good thing. location 747

Socrates had a mean, nagging wife; he always said that being married to
her was good practice for philosophy. location 805

Action

While you’re sleeping, traveling, attending meetings, or messing around
online, the same thing is happening to you. You’re going soft. You’re
not aggressive enough. You’re not pressing ahead. You’ve got a million
reasons why you can’t move at a faster pace. This all makes the
obstacles in your life loom very large. location 963

If we’re to overcome our obstacles, this is the message to
broadcast-internally and externally. We will not be stopped by failure,
we will not be rushed or distracted by external noise. We will chisel
and peg away at the obstacle until it is gone. Resistance is futile.
location 1003

Thickheaded and resistant to change, these are the types who are too
self-absorbed to realize that the world doesn’t have time to plead,
argue, and convince them of their errors. Soft bodied and hardheaded,
they have too much armor and ego to fail well. It’s time you understand
that the world is telling you something with each and every failure and
action. location 1104

The process is about doing the right things, right now. Not worrying
about what might happen later, or the results, or the whole picture.
location 1179

Everything is a chance to do and be your best. Only self-absorbed
assholes think they are too good for whatever their current station
requires. location 1203

An artist is given many different canvases and commissions in their
lifetime, and what matters is that they treat each one as a priority.
Whether it’s the most glamorous or highest paying is irrelevant. Each
project matters, and the only degrading part is giving less than one is
capable of giving. location 1206

We spend a lot of time thinking about how things are supposed to be, or
what the rules say we should do. Trying to get it all perfect. We tell
ourselves that we’ll get started once the conditions are right, or once
we’re sure we can trust this or that. When, really, it’d be better to
focus on making due with what we’ve got. On focusing on results instead
of pretty methods. location 1257

What setbacks in our lives could resist that elegant, fluid, and
powerful mastery? To be physically and mentally loose takes no talent.
That’s just recklessness. (We want right action, not action period.) To
be physically and mentally tight? That’s called anxiety. It doesn’t
work, either. Eventually we snap. But physical looseness combined with
mental restraint? That is powerful. It’s a power that drives our
opponents and competitors nuts. They think we’re toying with them. It’s
maddening-like we aren’t even trying, like we’ve tuned out the world.
Like we’re immune to external stressors and limitations on the march
toward our goals. Because we are. location 1455

You’ll have far better luck toughening yourself up than you ever will
trying to take the teeth out of a world that is-at best-indifferent to
your existence. location 1672

Will

A CEO calls her staff into the conference room on the eve of the launch
of a major new initiative. They file in and take their seats around the
table. She calls the meeting to attention and begins: “I have bad news.
The project has failed spectacularly. Tell me what went wrong?” What?!
But we haven’t even launched yet鈥?That’s the point. The CEO is forcing
an exercise in hind-sight-in advance. She is using a technique designed
by psychologist Gary Klein known as a premortem. location 1691

premeditatio malorum (premeditation of evils). A writer like Seneca
would begin by reviewing or rehearsing his plans, say, to take a trip.
And then he would go over, in his head (or in writing), the things that
could go wrong or prevent it from happening: a storm could arise, the
captain could fall ill, the ship could be attacked by pirates. location
1709

Not: I’m okay with this. Not: I think I feel good about this. But: I
feel great about it. Because if it happened, then it was meant to
happen, and I am glad that it did when it did. I am meant to make the
best of it. location 1874

Sometimes when we are personally stuck with some intractable or
impossible problem, one of the best ways to create opportunities or new
avenues for movement is to think: If I can’t solve this for myself, how
can I at least make this better for other people? Take it for granted,
for a second, that there is nothing else in it for us, nothing we can do
for ourselves. How can we use this situation to benefit others? How can
we salvage some good out of this? If not for me, then for my family or
the others I’m leading or those who might later find themselves in a
similar situation. location 1995

You can always remember that a decade earlier, a century earlier, a
millennium earlier, someone just like you stood right where you are and
felt very similar things, struggling with the very same thoughts. They
had no idea that you would exist, but you know that they did. And a
century from now, someone will be in your exact same position, once
more. Embrace this power, this sense of being part of a larger whole. It
is an exhilarating thought. Let it envelop you. We’re all just humans,
doing the best we can. We’re all just trying to survive, and in the
process, inch the world forward a little bit.